


The Scout

by Udunie



Category: Original Work
Genre: Abduction, Bondage, Breathplay, Captivity, Dirty Talk, Feminization, M/M, Mind Games, Original Character(s), Other Additional Tags to Be Added, Rape/Non-con Elements, Sex Toys, Shaving, Stockholm Syndrome, Training, commission
Language: English
Status: Completed
Published: 2015-09-29
Updated: 2015-10-11
Packaged: 2018-04-24 00:23:36
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 3
Words: 9,458
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4898341
Author URL: https://archiveofourown.org/users/Udunie/pseuds/Udunie
Summary: <blockquote class="userstuff">
              <p>Brian turned the heating up in his car. The cold was slowly getting into his bones, but it was the best time to be out on the job; no one who had anywhere to stay was out at this hour in the winter.</p><p>He followed the kid with his eyes, while simultaneously skimming over the file by the dim light of the street lamps. </p><p>Timothy Simmons, three months over 18, homeless. </p><p>He was a good candidate. Physically, he matched the specifications of the client and he hadn’t been on the streets long enough to pick up bad habits - not even turning tricks. Brian had no doubt that the boy would eventually resort to that, but if everything went well, he would be safely in Brian’s care by the time he got that desperate.</p><p>He shot of a quick text to a few of his contacts. Because seriously, why the hell should he wait? The kid was good enough, the trunk was empty.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

  * For [DiscontentedWinter](https://archiveofourown.org/users/DiscontentedWinter/gifts).



> This fic was prompted by the lovely DiscontentedWinter. It will have two more chapters, so stay tuned for more to come!
> 
> Beated by the lovely Emma - all remaining mistakes are mine, and mine alone!

Scouting was hard. Especially when the clients kept bothering Brian.

“Hello, sir, what can I do for you today?” he asked, trying to muster up some amount of friendly cheer. Playing nice was probably the hardest part of his job.

“Evening, Mr Smith. I just wanted to ask how the assignment was going,” the old man croaked, making Brian roll his eyes. It had been only a week and the geezer was already impatient. Quality work needed ample time - things had a tendency to turn ugly in his line of work if rushed.

“Everything is fine, sir. I’ve been looking and I managed to narrow it down to three kids,” he said. Not like he had an easy time, the guy had been pretty fucking specific.

The old man cleared his throat and Brian had the uncomfortable feeling that the pervert was actually getting hard. Some of his clients were disgusting.

“I need a cute one, Mr Smith. Someone… charming.”

Brian stifled a put upon sigh. Yeah, yeah, he knew that. Under twenty, pale, brown eyed, skinny. It was all in the assignment details.

“Yes, sir. I remember,” he knew he had to somehow calm down the guy, otherwise he wouldn’t get anything done tonight. “I actually have a pretty good match, but I still need to check out a few details. Believe me, you don’t want to end up with a junkie.”

The client hummed.

“True. How long is it before you can deliver?”

They also discussed that. In detail. People were insufferable.

“Well, if you still need me to break him in, it will take anything from a few weeks to roughly two months. I’m working with brought material here. Of course, if you changed your mind and want to break him in yourself…”

“No, no, Mr Smith. I’m afraid I don’t have that much excess energy,” the client put in quickly, making him smile. Sure. The guy was somewhere between eighty and death.

“In that case, sir, I would better go and make sure you get your boy as soon as possible,” he said, hoping to get this conversation over and done with. Especially since he just saw one of his potential marks turn the corner.

“Yes, yes that would be best, Mr Smith. Keep me updated on your progress.”

“Of course, sir,” he said before disconnecting.

He opened the folder in his lap. Which one was this again? Ah, right. Timothy Simmons.

 

***

 

Tim was having a pretty fucking awful day.

Being homeless was not a walk in the park, not even on the ‘better days,’ but when it got this cold and the shelters were full, it was harder than he’ve ever imagined.

Not like he became homeless because of some stupid hippie, anti-capitalist bullshit - it wasn’t exactly his choice. His parents were clear about the fact that they would only do the bare minimum by letting him stay until he turned eighteen - if he continued with his ‘lifestyle’.

Fuck them.

And fuck this stupid, freezing weather in particular.

Seriously, all he wanted was a warm place to stay and some food to eat. Preferably with dessert. Shit, he was at the point where he would have given anything not to be out here, waiting to die from hypothermia.

Even though his life was not exactly a fairytale, Tim should have known to be careful about what he wished for.

 

***

 

Brian turned the heating up in his car. The cold was slowly getting into his bones, but it was the best time to be out on the job; no one who had anywhere to stay was out at this hour in the winter.

He followed the kid with his eyes, while simultaneously skimming over the file by the dim light of the street lamps.

Timothy Simmons, three months over 18, homeless.

He was a good candidate. Physically, he matched the specifications of the client and he hadn’t been on the streets long enough to pick up bad habits - not even turning tricks. Brian had no doubt that the boy would eventually resort to that, but if everything went well, he would be safely in Brian’s care by the time he got that desperate.

He shot of a quick text to a few of his contacts. Because seriously, why the hell should he wait? The kid was good enough, the trunk was empty.

He had a lot of informants; police officers, social workers, volunteers in local shelters… He wanted to see if sweet little Timmy had any baggage before making his move.

He tracked the boy in the mirror, seeing him enter a decrepit building - probably looking for a place to stay the night. Good.

Brian didn’t have to wait long, and two of his contacts texted back. He couldn’t have gotten better news. The kid appeared to be clean, no friends, no worried family, no debt collectors on his tail.

And he wouldn’t be missed by a single soul.

 

***

 

Tim had no idea what was going on.

He remembered holing up in an abandoned building - he had trouble falling asleep, because it was so fucking cold, but then… Then nothing.

All he knew was that his head was hurting. And it was dark.

It felt like his skull was stuffed full of cotton, so it took some time to make sense of his surroundings. He was warm, lying on something that was soft enough to be a real, actual bed so at least that was something.

He tried shifting around, but found that it was difficult. Tim tugged on his hands and legs in vain - it seemed that both his wrists and ankles were tied to the corners. Fuck.

It was probably a good time to panic and he did feel his stomach knotting itself into a ball of worry, but. He was just so, so tired. He had been tired and hungry and cold for days and simply didn’t have the excess energy for luxurious things like working himself into a frenzy. If he wanted to be completely honest, he always knew that he would end up in a ditch somewhere - what with his nonexistent survival skills.

Tim decided to take stock of his senses one by one, hoping to figure something out.

His brain struggled to tell him that this apathy was not normal; there was a strange, chemical aftertaste in his mouth that he couldn’t identify, so that might have had something to do with it. Or it might have been the gag, because of course he was gagged. Not good.

First, he tried opening his eyes, but wasn’t able to; his lashes brushed against something solid, so he was probably blindfolded. Not good at all.

He tried listening next, but everything was strangely muted. Tim flexed his jaw and could feel that there was something in his ears too, blocking his hearing and leaving only the echo of his blood rushing in his ears. Very not good.

Fuck. He was going to get killed. He worked his brain, but couldn’t come up with a single reason why he would be laid out like this if it wasn’t the work of some wacky serial killer. He didn’t hear about one in the city, but truth be told, he didn’t exactly have access to the latest news.

Tim swallowed. It was awkward with the gag - some kind of ball, made of rubber, maybe - forcing his jaw open, but his throat was dry.

He didn’t expect to be touched, and he almost jumped right out of his skin when something - or someone - brushed against the sensitive skin of his belly. He shouted instinctively, but the sound got mangled through the obstacle in his mouth.

Apparently, he was also naked.

The… the hand stayed there, resting on his stomach. It was warm.

Tim tried to get his breathing under control; hyperventilating wouldn’t have gained him anything.

He had to stay calm.

The owner of the hand must have been waiting for him to do just that, because as soon as he managed to calm down a bit the hand started moving. It didn’t do much, just slid up and down his body; from under his navel up to his collarbone, slow and  easy. It still managed to make him break out in goosebumps.

It was pretty terrifying that he couldn’t… That he had no idea that someone was even there. If not for that touch, he would have no way of knowing that he wasn’t alone.

The bed - or mattress, or whatever - dipped as his captor sat down beside him. It was weird how acutely he was aware of the jean clad thighs pushing against his side. It was like his skin was suddenly relaying information in high definition.

It was stupid. Really, it was, but after a time he couldn’t help getting used to the touch. As outrageous as it sounded, there was something soothing about it. It had to be a trick of his brain, latching onto the only contact he had with the world, but. In this dark, silent reality he was thrust into that warm touch felt almost like an anchor.

 

***

 

Brian was pleased.

There was a reason why he liked working with homeless people; they were usually so starved - not just for food, but also for simple, human contact - that it took ridiculously little to make an impression on them.

The not being missed by anyone part was also a bonus, of course.

The kid was good. He fit the client’s specifications well - pale, creamy skin, a sweet little pink mouth and long, elegant limbs. As far as Brian was considered, the constellations of beauty marks he had worked out wonderfully as well; they gave the boy a bit of uniqueness.

He was easy to catch too. All Brian had to do was sneak up on him with the classic drug soaked rug and ta-da! mission accomplished. Well, half of the mission.

Looking at the boy now, Brian was kind of annoyed that he would eventually have to give him up. As embarrassing as it was, the client’s taste just happened to match up perfectly with his own. But, he was already paid, and business always comes before pleasure.

That didn’t mean he wouldn’t be enjoying training little Timmy. Oh, he would.

It took him about twenty minutes to get the boy all pliant and relaxed just by simply petting him. That was a good sign. Usually at this point most of the people he worked with were still panicking big time, making everything harder on both themselves and Brian.

It was time for phase two.

As cute as the kid was, he was still, well… a homeless person. He obviously tried to keep up with the personal hygiene, but that was not something easily accomplished, especially not in the colder months.

Brian could have bathed him before he woke up, but he didn’t want to tempt fate. Sometimes people reacted badly to drugs, so he tried to use a small dose - just enough to get them home and the merchandise decked out on the bed.

And getting a sponge bath most of the time proved to be an important step in bonding, anyway.

He patted the boy’s stomach before standing up and getting the stuff he needed. He didn’t hurry, knowing that every minute Timmy spent alone just made him more desperate. Brian got a basin of warm, soapy water and a washcloth, humming under his breath.

After a second of consideration he also picked up the straight razor he kept for special cases. He didn’t often use it, since it required a certain type of person to react positively to it, but somehow he felt like he could take the chance with sweet little Timmy.

By the time he returned, the kid was all tense again, but that was okay. He had to learn to relax whenever Brian was touching him. He started with the washing. The boy startled at the first brush of the wet cloth against his skin, but a few minutes later his muscles slowly lost the tension.

Very good.

Brian made sure that he kept everything light and easy. That didn’t mean he wasn’t thorough, but this was mostly about bonding, about making the kid feel like he was being cared for.

He could practically see as Timmy melted under the careful attention. Depriving him of his senses made sure that he was unable to concentrate on anything but Brian and convinced his brain that he was the only one he could count on.

After he got the boy more or less clean, he picked up the razor. Brian grabbed the kid’s leg, holding it down securely.

This was pretty crucial.

He smeared a bit of shaving creme on Timmy’s shin and then carefully - so very carefully - ran the razor over it. He could feel the second the boy realized what was happening, because he went stock still, not even daring to breath for a second or two. Excellent.

Having him aware of the danger was important, and dear little Timmy wasn’t stupid. But, with every bit of skin shaved, Brian was gaining his trust.

Here he was, someone with all the power over the situation, with a potentially deadly weapon in his hands, and he wasn’t hurting him. Now, some people just couldn’t process that, their minds stuck on the danger part, but some of them - like this kid - reacted beautifully, and ended up building the kind of trust that can’t be forced on someone. Just what Brian wanted.

 

***

 

Tim was scared shitless. Or at least, he was, at first. The guy - for some reason he was pretty sure it was a guy - was shaving him, and not with a disposable razor either. His stomach was heavy with dread, but to his surprise he didn’t get cut into bite-sized pieces like he feared.

It appeared that his captor just wanted to have him hairless.

Tim had a hard time making sense of that information. It probably didn’t promise good things to come, but the fact that he wasn’t in imminent danger still sent a wave of relief washing over him.

When the guy untied one of his legs to be able to shave it properly he considered kicking out and trying to get free somehow, but thankfully he remembered the razor just in time. Kicking out blindly was not a good idea.

As strange as it sounded, he felt even more vulnerable with his feet untied. Maybe it was because he knew that - theoretically - he could fight and still decided not to. He couldn’t stop shivering.

The guy was careful, holding him still, but not gripping too strong, and when he was finished with a strip of skin he would wipe the excess foam off and smooth his palm over the freshly naked skin. It was… fuck.

Shit, Tim was in so much trouble.

 

***

 

It took more than an hour for Brian to finish with the shaving. It was fine, he liked to take his time, especially at first, when the merchandise was all fragile and impressionable. And Timmy was actually a pleasure to work with.

Brian was seriously tempted to mentally high-five himself. By the time they were finished and the boy was as smooth and soft-skinned as a little girl - just like he needed to be - the kid actually got an erection.

He didn’t tie his legs back to the bed. For now, it was enough to keep touching him and the boy stayed pliant and relaxed. Brian shifted closer and closed his fingers firmly around the boy’s cock. Of course, Timmy gasped - as much as he could behind his gag - and twitched, but didn’t try to move away from the hand, even when Brian started jerking him off.

Very, very good.

In his head, Brian went over the client’s training requirements. It was never too soon to start conditioning, but he couldn’t exactly start with something too traumatizing.

Oh, yeah. The old goat did ask for the boy to be able to come just from choking on a cock. That was easy enough.

As far as he could see, the kid had a submissive streak a mile wide. Or a penchant for fear-boners. Same difference.

Usually, Brian had to use drugs to get them to enjoy things, at least at first, but Timmy was aroused, even though he had been kidnapped by a stranger who spent the last hour shaving every inch of his body.

He couldn’t help smiling to himself. He always knew that he had a knack for picking the cream of the crop. But then again, it was why he made scouting his full time job.

Timmy was getting closer and closer to the edge, it was amazing to see the way he started flushing. First, it was just his cheeks turning ruby and charming, but then the blush slowly crawled down his neck until it covered the top of his chest. Sweet boy, this one.

Brian waited until the last moment, drawing out the kid’s pleasure with practiced, easy strokes. He had enough experience to see the boy’s orgasm approach well in advance, and he was determined to make the most of it.

He reached up and pinched Timmy’s nostrils together, cutting off his air - the gag was big enough that he couldn’t breath through it. The effect was instantaneous.

The boy started kicking and struggling - Brian made a mental note to train that out of him at one point -, back arching off the bed. It was completely fine. Brian didn’t stop jerking him, speeding up his movements with every second.

By now, the kid’s adrenalin was probably through the roof.

Before it got too dangerous, Brian did the little twist-and-tug move that always worked like magic and sure enough, Timmy was coming, his cock twitching like a living thing between Brian’s fingers.

As soon as he started coming, he let go of his nose, allowing the boy to suck in a few noisy breaths.

Brian smiled, wiping his hand on the bedsheet.

If he did this enough times, Timmy’s brain would connect pleasure with not being able to breath - and his body would also learn that if he came he could breath again.

Piece of cake, really.

 

 


	2. Chapter Two

Brian might have made a terrible mistake.

Really, he should have know better; just because Timmy had been admirably responsive, he shouldn’t have underestimated him.

They had been doing good, Brian had him eating out of his palm - literally - they even got to the point where he allowed the boy to roam the basement when he had things to do elsewhere. Of course, Timmy had to wear mittens and a leather hood that cut off his hearing and sight, so really, he was just stumbling around on all fours, but still. It was a good seven days.

Until that fucking phone call.

Of course, it was Brian’s fault - he had been so sure that he managed to fuck Timmy into exhaustion that he made the mistake of putting the client on speaker.

It ended as disastrously as expected.

Who knew the boy wouldn’t take well to learning that he would end up as the ‘pussy boy’ of an old geezer…

 

***

 

So, naturally, Brian had to start using a firmer hand. It was such a shame, he almost felt bad for the boy, considering that it was his fault that things went pear shaped, but… little Timmy had to find out the truth sooner or later.

He sighed, sitting down beside him. The shock collar might have been a bit much, but he was forced to take Timmy’s mobility privileges away… There was a sensor under the bed, and it reacted whenever the boy tried to get of it.

Brian really loved technology.

Timmy had his hands tied to his collar. He was still wearing the mittens to stop him from trying to fiddle with the electronics and well… he seemed pretty pissed, even with the blindfold covering half his face.

Brian ran a hand through his hair, frowning when the boy stiffened at the touch, and then plucked out one of his earplugs.

“Alright, baby girl. Time to see if you'll get fed today…” Brian told him. He had a platter of bite sized food at the ready but he wasn’t too optimistic.

He was pretty sure that the boy was truly starving by now, still, not cooperating meant not eating as far as he was concerned. He had no doubt that the boy was as stubborn as a teenager could be, but he had enough experience under his belt to know that survival instinct always won out in the end.

He carefully unbuckled the gag from around Timmy’s head before putting the earplug back in. There was no need to let him experience more sensation than absolutely necessary. Being able to see, hear and move was a privilege and his little bitch didn’t earn any of them.

Brian sighed somewhat warily - now that the boy couldn’t hear him - and brushed the back of his fingers across those lovely pink lips. He was ready to wrench them away if Timmy tried to bite him again. Not like he haven’t enjoyed the beating he doled out afterwards, but that didn’t mean he liked the disobedience.

For a second it looked like the boy would just refuse to react - no punishment needed in that case, though no food would be eaten either - but then, slowly that soft, cute little tongue sneaked out, licking at him delicately.

That was just wonderful. Brian couldn’t help giving the boy a proud smile, even though he couldn’t see it. They seemed to be back on the right track.

He let Timmy work on him for a bit more before pushing two fingers into his mouth, enjoying the reluctant suction. He couldn’t help himself, really. Brian fucked the boy’s mouth for a few moments, pushing in as deep as he could. There was some gagging, but not as much as when they’ve first started. Good.

When he was finally satisfied, he fed the boy. He went slow, giving him sips of water between bites, not wanting him to get sick. Still, it didn’t take long for all the food to be gone.

Just like expected, by the time his tummy was full, Timmy seemed much less sullen.

Brian put his gag back, but took the earplugs away. A bit of a positive reinforcement was in order.

He stroked the boy’s hair again, and this time, there was no flinching either.

“You are a very good girl,” he said quietly, knowing that Timmy’s ears must be very sensitive after being cut off for a week. “You will make someone a proud daddy.”

Maybe it was tiredness, maybe it was lethargy, but the boy didn’t work himself up over the comments.

Just as well.

 

***

 

After their daily cleaning ritual - Brian didn’t particularly enjoy it; giving enemas was not his cup of tea, even though it was an excellent source of humiliation - he decided that they needed to get back on schedule with the training.

He disarmed the boy’s shock collar and made him sit up before getting the ballet boots on him. They were incredibly restricting, forcing the wearer to walk on their tippy toes. Probably very painful, but that wasn’t his problem.

If Timmy learned to walk on those, he would have no problem with regular high heels.

He laced the boots on, enjoying the boy not fighting him for once. Of course, Timmy didn’t know that the collar was inactive, and he knew - from bitter experience - that Brian had a remote, so it might have been that. Whatever.

Because Brian was never one to give up a chance to hit two birds with one stone, he also got the pretty, black leather corset out of the toy chest. Good posture was important, and a slim waist even more so.

He pulled the strings as tight as he dared, until the boy could only take shallow, quick little breaths. As a very welcome side effect, Timmy slowly got hard. Brian was pretty sure his body would never be able to separate the lack of oxygen from pleasure. But well, that was kind of the point.

“Alright, come on, girl, up you go!”

It was hard to get the boy on his feet; for a few seconds he couldn't find his balance, and even when he finally managed he just stood there with his muscles shaking from the unnatural position.

That just wouldn’t do.

Brian got out his riding crop and hit the boy’s ass hard enough that he almost fell. Of course, he wasn’t about to let the merchandise get damaged, catching him by the elbow and keeping him upright.

“Now, now. Little pussy boys need to know how to walk properly, so you’d better get to it,” he said. Timmy didn’t react, just whined through his gag. Brian slapped his ass again.

The boy did stumble again, but also took a tiny, precarious step forward.

“Excellent. Keep going. I will tell you when you reach the wall. Come on, be a good little girl…”

 

***

 

Tim’s whole body hurt.

His ribs felt bruised, even after the man took the corset off and his feet were killing him. And his ass… Shit. His whole backside was burning with how many times he’d been hit.

He was so exhausted that he just lay on the bed, unmoving. The guy could have done anything with him right then, and he probably couldn’t have moved a muscle.

It was a slow realization, but he started to understand that he wouldn’t be getting out of here. This… This was his life now.

It hurt his head just to think about it.

Tim knew that he didn’t want this, but… he wanted to eat. He wanted to hear and see and fucking move, but he was only allowed when he was being ‘good.’

So. He had no way to escape and no way to make things stop happening. Was it… Was it so bad that he considered just giving in? It wasn’t that awful, really. Okay, yeah. He got spanked and choked and had to learn how to suck a cock but in exchange he had food and a place to stay - everything he ever wished for just a few days ago.

Maybe… maybe if he could stay here, with the man… He didn’t know why, it didn’t make any sense, but he felt like that would be better, safer somehow. Of - fucking - course, he knew now that he wouldn’t be allowed to stay. That other man - the old one - who was on the phone with his kidnapper was going to buy him.

He was going to be his ‘pussy boy’.

As much as he hated the thought, he couldn’t do anything to avoid it.

The man sat down beside him, taking his gag out and letting him take a few sips of water.

Tim... wanted to finally see his face.

After he drank, the gag was put back in place, but the earplugs didn’t return. Tim was strangely grateful for it.

“You did good, such a sweet little girl when you’re not sulking,” the man said, stroking his cheek. His hands slid to his neck, fiddling with his collar for a second.

Tim didn’t even want to think about what that meant. The first time he was electrocuted, he was so scared... But as long as he stayed on the bed, nothing happened. That was good. He didn’t want to get hurt.

The man shifted on the bed. He lifted Tim’s leg and slipped between them. His cock was hard and it was pushing against his hole.

Tim shuddered. The man never fucked him before - he used some toys on him and put his fingers in his ass every morning, but he never used his dick. It should have made him freak out. For some reason, it didn’t.

If… If he wanted to be honest, he had more orgasms in the last week than he did since he got on the streets - being homeless didn’t exactly offer up too many private moments. He couldn’t help that his body was kind of… responsive.

“Alright, pussy boy. Let me butter your cunt up a bit,” the man said.

Tim heard a bottle clicking open, even the sound of the lube being squirted into the man’s palm. It was weird how sensitive his ears became even after such a relatively short time of disuse.

“Now, we are going to cover ‘Getting Fucked 101’...” he said. The blunt head of his cock was back, this time slick and slippery. “First lesson: you are a pussy boy. pussy boys have lewd little cunts, always hungry for cock. That means that you won’t be pampered and stretched, you get a bit of lube and that’s it.”

Tim swallowed, feeling his body tense up. There was no way he could do that.

“No, no, no,” the man tutted. A second later Tim winced in pain as his nipple was twisted, hard and sharp. “Locking up your muscles is something you’re absolutely not allowed to do. You need to relax, honey. Breathe slowly and concentrate. It goes in either way - you decided how much it will hurt.”

Tim shook his head desperately, unable to do anything else, but… The man’s cock was pushing against his entrance, the pressure growing more forceful every second. Fuck. Fuck-fuck-fuck...

He tried doing as he was told, tried to force his hole to loosen. It felt like it did - but only a tiny bit.

“Hm… Something like that. If you think that old geezer will give you time to adjust every time he feels like putting that wrinkly, withered prick of his in your cunt, you are sorely mistaken.”

Tim felt his whole body flush at the words. The way the man talked about his future, like it was nothing out of the ordinary, somehow just made him more ashamed of it, even though it made little sense.

He bit down on his gag and concentrated, managing to relax his muscles another fraction more. The tip of his kidnappers cock pushed inside - not even the whole head, but still, Tim had to stop and breathe. It hurt. It wasn’t horrible exactly, but the burn was intense and overwhelming.

“That’s what I’m talking about! Almost there, little slut. Now. One easy way to do it is to bear down, just like when you take a shit. You’ve been cleaned out, so there’s no danger of you soiling yourself, hm?”

Tim wasn’t sure he could do that. He… He just couldn’t. There was some inherent humiliation in the motion of pushing…

The man didn’t wait long before he clucked his tongue in disappointment.

“Well, I won’t force you… Let’s try it the hard way, then,” he said, before giving a push that would have made Tim scream if not for his gag. It only lasted for a second, but the pain was blinding. The man couldn’t push inside, but it seemed like that wasn’t even his plan.

“I’m going to tire your sphincter out; I will push and then stop. It will be painful as hell, but since you can’t be assed to do it the simple way, I don’t particularly mind.”

Tim gave a pathetic little sob when the man did it again, pushing against him painfully until he felt like his flesh would tear and pulling back in the very last second.

It only took a few more tries to have him covered in sweat. It was hard to breathe, his chest heaving with the periodic waves of pain washing over him.

It worked, to some extent. He could feel as his hole slowly but surely lost some of it’s resistance. It still wasn’t enough for the man to push in without causing damage, but it was only a matter of time.

“Okay, honey. I bet this isn’t fun for you,” he said as he pulled back to put some more lube on his dick. “So, I will give you one more chance to try bearing down.”

Tim swallowed. The inside of his blindfold was wet with tears. As much as the idea still made his belly squirm, he really didn’t want to do this any longer.

When the man lined up to his hole again, he sucked in a breath, let it out slowly, and pushed.

To his shock, it worked. It worked so well, that the head of the cock popped in on the first time, and from then it was easy. Well, it was still painful, but the man didn’t stop once he was in, and bottomed out in one slow, smooth motion.

“Now that’s what I like to see! Good girl,” he said, and Tim could hear the smile on his voice. “Let me give you a bit of a reward.”

Tim moaned as he felt the man lean forward, jostling the dick lodged into him. Deft fingers made quick work on his gag, and a second later it was out. He was given a sip of water and a pat to the cheek.

“Second lesson. You have to be loud, and I don’t mean talking, not yet, anyway. No matter how abysmal a fuck is, you always have to act like it’s the best ride of your life. Nobody cares how you are feeling, honey,” he said, voice gentle.

Tim licked his lips. What. What did that even mean?

The man pulled back until only the fat head of cock was inside and then started fucking him in earnest, making his breath hitch.

“Come on, bitch. You have to sound like you’re enjoying it,” he explained. When Tim didn’t react fast enough, he twisted his nipple again, forcing a cry out of him.

“Don’t make me punish you, honey. You’re smarter than that…”

Tim licked his lips. Fuck it.

On the next thrust he moaned, quiet and tentative. It sounded awfully fake to his ears, but the man was apparently happy with it, because he hummed under his breath and circled his hips, making him see stars - the good kind, for once.

Tim did it again, his voice gaining volume with every groan, until he was obscenely loud. It was weird, but the more he did it, the more he actually got into it. There was still shame, but… it felt good to finally be able to express himself some way.

“That’s it. That’s what I want to hear; a bitch in heat. I bet you wouldn’t care right now if someone just walked in and took my place, hm? You’re happy as can be as long as you have someone to stir that slutty pussy of yours.”

Tim was… shocked to notice that he was actually hard. He… did he actually enjoy it? He wasn’t sure anymore. He didn’t want to examine why his brain refused the thought of a ‘stranger’ doing this to him...

The man kept fucking him, his hips moving faster and faster.

“Third lesson, honey. When your partner is getting close, you have to milk their cock. It’s not fair that they are the only ones working when you’re the one who’s gagging for your cunt to be filled with come.”

Tim moaned. He couldn’t tell if it was fake or real anymore. It might have been the words, but his body clenched down on it’s own accord, making the man grunt.

“Just like that, that’s how a good little pussy boy does it,” he said. “Give me more of that, honey.”

Tim did. He didn’t know what was going on with his body anymore, but honestly? He was past the point of caring.

He squeezed down, chasing that elusive feeling of the man’s cock brushing against his prostate. He did it again and again until the man above him jerked and came to a stop.

Tim could feel the way his cock twitched deep inside him, squirting out thick ropes of come.

He couldn’t stop shivering. As much as it was unsettling, he was close to coming too - even though his own dick haven’t been touched since they’ve started.

The man huffed out a breath and straightened out from where he doubled over in pleasure. He pulled out with a satisfied sigh. Tim groaned, it was too fast and his hole stayed gaping even after the cock holding it open was gone. There were fingers prodding at him, dipping into the abused ring of muscle.

“Now that’s what I like to see. You did good, honey, and I’m never one to deny a reward when it’s well deserved, so, here,” he said and just like that, he pushed something into Tim, making him gasp.

It was hard… maybe plastic. Kind of egg-shaped, and it disappeared into his ass completely.

His hands were untied and then fixed to the bedposts, followed by his legs, until he was lying spread on top of the covers.

The mattress shifted as the man stood, picking something up from the bedside table, a second later the toy started fucking vibrating.

Tim’s back arched off the bed, mind going hazy immediately from the too-much-not-enough pleasure.

“Fourth lesson: if pussy boys even get to come when they're fucked, they come with their cunts.”


	3. Chapter 3

Brian wasn’t exactly nervous, but he did feel a certain sense of excitement.

No wonder, it was his sweet little Timmy’s graduation day.

He could hardly believe that it’s already been two months. Not like he didn’t work a lot to get them where they were right now, but still. He was kind of sad that it was all coming to an end.

For now, he didn’t have much to do, just sat in his chair and watched the boy get himself ready. He expected Timmy to demonstrate everything he had been thought, and hygiene was one of those things.

The basement had a tiled corner with a shower and everything a girl could need - without curtains or anything else to block the view. The boy was already finished with washing himself - inside and out - and he also shaved. It was important for pussy boys to be smooth and soft everywhere.

Brian watched Timmy stretch his cunt. He used a generous amount of lube, pushing some of it straight into his hole, knowing that it would be all he got tonight. Being nice and sloppy was equally important.

The clothes came next. Brian already laid out quite a few for him to chose from. He knew that the old man would likely pick his little girl’s clothes out himself, but that didn’t mean the boy didn’t have to know how to dress up for a special occasion.

Timmy didn’t think too long. He picked out a neon pink thong with a matching lacy bra. Then, a leopard printed, form fitting dress with a deep neckline that barely covered the swell of his ass.

Good.

Brian was already satisfied, but when the boy picked up a pair of thigh-high fishnets, he couldn’t help humming in satisfaction under his breath. Today’s theme was cheap entertainment and Tim was nailing it.

Lastly, he pulled a pair of hot pink platform shoes up to finish the picture. They would match his undies.

For a second, Tim glanced over at him, but Brian didn’t let anything show on his face, the boy had to perform on his own for once.

Timmy looked at himself in the mirror and licked his lips. Brian was delighted to realize that the boy was actually a born crossdresser, who actually found great joy in being feminized and humiliated. All he had to do was polish those urges up a bit and scrub off all the needless modesty.

Make-up was next.

That actually took the boy ages to learn. Not because of some deep-rooted sense of shame, oh no. He just lacked the skill for it. Brian had to make him try again and again until he finally managed to do a good enough job. It wasn’t really street appropriate - the mascara too much, the eyeliner too thick, but well.

Timmy knew by now that the best part of a blowjob was seeing the way his tears made his make-up run.

The blood-red lipstick was a must, of course.

Brian couldn’t help shifting in his seat. Sure, he knew every little trick Timmy would use, he was the one who taught him, after all, but that didn’t mean his cock wasn’t just aching to be in the boy right that second.

The old man would be really lucky. Brian kind of hoped that he would bite the dust soon so he could maybe get the boy back.

Last but not least, Timmy rooted around in the small basket filled to the brim with accessories. There was nothing valuable in there, Brian picked them up in dollar shops mostly - cheap, plastic things - but the aim of tonight wasn’t to look sophisticated.

The boy chose a bright green, almost yellow, really, pearl necklace and a cute head-band with a large pink bow on one side.

Oh, that looked delicious.

Timmy gave himself another, last, look in the mirror before he turned towards Brian, smiling coyly. He took a few steps, stopping by the cd player off to the side. His second test was choosing the music.

 

***

 

Tim’s fingers twitched between the cds, he had to chose the perfect one… He needed to please Brian. It was strange, even though he knew that if he managed to do just that he would be sent off to the buyer, but he just…  wanted to make Brian proud.

Brian taught him so much.

Sure, he couldn’t leave or do things that were inappropriate for a pussy boy, but he was… happy. He knew what he needed to do, knew how to behave, how to be what people wanted… Brian gave him pleasure and rewarded him when he was good. He made Tim see that this was where he belonged; serving a man. A real man, not just a needy bitch with a dick like he was.

He knew how to dance. That wasn’t the problem. By now he could have danced to any of the songs on the cds, he even had favorites, but this wasn’t about what he wanted. Tonight, Brian wanted a campy whore to entertain him, so Tim had to be just that.

He could do it for Brian.

He wasn’t sure he picked right, but when he finally popped the cd into the player and turned to face Brian again he was greeted with a satisfied little grin. Apparently I’m a Slave 4 You was a hit. Then again, nothing screamed campy like Britney Spears.

He sauntered up to the man, taking care to sway his hips and take small steps. He could walk in high heels without a problem, but he needed to be sexy now. He always needed to be sexy.

There was a bulge in Brian’s pants that made his mouth water. He almost stumbled for a second, but only because he wanted to have at that dick so much. He loved Brian’s cock. Oh, sure, he loved any cock, really - he was supposed to, as a pussy boy, after all - but he loved Brian’s the most, he probably knew it better than his own.

He closed his eyes and just concentrated on the music, letting the beat wash over him. He’d learned the best way to pretend was to not pretend. It wasn’t hard. Especially when he could practically feel Brian’s eyes on his body.

He started moving. Slowly at first, twisting his hips and shimmying this way and that. His hands found their way to his body, smoothing over his chest, stopping to twist his nipples through the layers of fabric. He loved when his nipples were hurting.

When Tim was sure that he got the hang of the music he opened his eyes, looking straight at the man in front of him. He wasn’t always allowed to look him in the eyes, most of the time ordered to keep his gaze averted, so he wanted to make the most of it.

Brian was good looking. He had a bone structure to die for and his neck… Tim loved his neck. He loved everything about him, really; his dark hair, the blue of his eyes that stupid little beard… Everything.

He danced closer, running his own hands over his chest - where he wanted Brian’s hands to be - but he didn’t go anywhere near his dick. Pussy boys didn’t play with themselves, that was only for their men if they were feeling generous.

He twisted his body down-down-down until he was crouching in front of the man and then finally allowed himself to touch Brian, rubbing his palms up and down those strong thighs, stopping just short of his crotch. He had to tease.

Brian gave a little hum, reaching out and hooking a finger into his necklace, pulling him up until he was hovering just an inch above his lap.

Tim knew better than to grind down. He was so, so hard and it was the only thing he wanted, but he couldn’t. He wasn’t allowed relief and he knew it. So he did the next best thing, putting his arms around the man’s shoulders and kissing him with his mouth open, listening to Britney Spears moaning in the background.

It was amazing. He kissed sloppily, just like was taught - with too much tongue and too much saliva - like the needy whore he was - pulling Brian’s tongue into his mouth and suckling on it like it was the best thing he ever tasted. It kind of was.

Brian’s hands grabbed his hips, jerking him closer until their chests were flush together and held him there with one hand while the other sneaked under his dress, fingers biting into the meat of his ass. He squeezed down hard, making Tim hiss. His ass was still sensitive a bit from the spanking he got yesterday, but Brian was a firm believer that pussy boys should get at least a bit of discipline every day.

When they had to part to breathe Brian’s hands left him. It was a sign to move the show along so he did. Tim turned around, sitting down on the man’s lap and rubbed his ass against his erection, feeling that hard, hot bulge slide between his cheeks.

He reached back, grasping at Brian’s hair and pulled his head to his neck. It might have been a bit selfish - he lived for getting bitten hard enough to bruise - but he was supposed to be needy right now.

 

***

 

Dear little Timmy was exceeding all of his expectations. He was everything he ever wanted; beautiful, obedient and submissive. His sweet, slutty pussy boy.

It was a shame he had to give him up, because - let’s be honest - the second Timmy started the music, he knew he would pass any and all tests he could make up. Not for the first time, Brian wished the old fucker would die in a fire. He had other assignments lined up, so it wouldn’t be a struggle to pay him back… but it would surely ruin his ‘reputation’. It was though when his job was also his passion.

He had no idea what it was about Timmy that made him want to keep him, but there was no doubt about it. He wanted the boy like none of his previous protegees before.

Timmy took that moment to grind against his cock just right, making Brian moan. Fuck. The boy was good.

Timmy danced, body moving languidly with the music. He was doing an excellent job of driving Brian mad.

He had a feeling that it was kind of a shock for both of them when the music finally ended. To his credit, Timmy didn’t drop character, but just sat on Brian’s lap, hips twitching back into him.

“Did you like my dance, mister?” he asked, hand still tangled in Brian’s hair.

“Mhm, I sure did… Did you like to give it to me, little bitch?”

Tim shuddered, giving a tiny moan.

“Yes. I love to please you.”

Brian hummed. Excellent answer.

“I’m glad to hear that. Any idea of what we should be doing next?” he asked, biting into the boy’s neck. His teeth clenched down hard, just shy of breaking the skin. Timmy gasped, body arching against his own.

“Yesss! P-please… Please fuck me! I… I want to feel your cock in my p-pussy,” the boy pleaded, voice sweet and completely honest. Brian taught him well. Sometimes he was afraid that a little too well - it wasn’t right that even he couldn’t withstand Timmy’s charm.

“We could do that, but first, you have to let me up,” he said, smiling into the boy’s neck. He blew gently on the saliva wet bite mark, enjoying the way Timmy trembled.

“Yeah.”

Timmy stood, turning fluidly to pull him up by the front of his shirt.

Pushy, pushy.

The boy stepped close, kissing him again. He was almost taller than Brian in the heels, but he didn’t mind. As much as he enjoyed Timmy playing the little bitch, he still wanted to know that there was a boy under all the make-up. Knowing that he managed to make him into such a cock-loving whore was half the fun.

Timmy backed away reluctantly after their kiss was over.

“Please let me ride you, mister, I want to feel your cock in my belly,” he whispered, and who was Brian to say no to that?

He lay back, folding his hands under his head to get comfortable. He would not be the one to do all the work tonight.

Timmy bit his lip adorably before climbing on the bed, staying on all fours so he could bend down and take Brian’s zipper in his mouth, opening his fly slowly.

Brian didn’t think he would ever forget the picture his sweet little slut made in that moment. If he hadn’t already been painfully hard, that alone would have got him going. Timmy smiled, rubbing his cute, upturned nose against his bulge before finally unbuttoning Brian’s jeans to free his cock completely.

“Do you like what you see?” Brian asked, already knowing the answer.

“Yes, mister. I’m already so wet, I’ve soaked through my paties,” Timmy moaned as he straddled his hips, pulling the hem of his dress up to show it off.

His cock was hard, with a wet patch dampening the fabric of his thong by the head.

“Lovely, little bitch. Now show me how well you can take a cock.”

Timmy nodded eagerly and got into position. He didn’t bother with taking his underwear off, just pulled the string at the back out of the way before grabbing Brian and lining him up with his hole.

He sank down slowly, barely even pausing at the stretch. Brian wasn’t ashamed of the moan forced out of him. His sweet little pussy boy felt amazing.

Timmy stopped when he was completely seated on the thick cock and just panted with his mouth open.

“Come now, honey. It’s not nice to make paying customers wait,” Brian chided, shifting his hips a bit to get the boy going.

“I’m so sorry.… I just. My pussy has been empty for so long, your cock feels amazing…” he said, opening his eyes. He arched back and planted his hands on Brian’s knees to get some leverage before lifting his body up and the dropping down again.

Brian couldn’t help hissing - the boy wasn’t fucking around, getting to rough and fast in only a few seconds.

“So good, so good, so good,” he moaned between breaths, his head thrown back as he rode Brian’s cock like the pro that he was. Amazing what a mere two months could achieve.

“Yeah, honey, just like that. Show me your tits, I want to see you play with them,” Brian said, just to distract himself from coming - otherwise their little exam would be over way too soon.

He watched Timmy’s long pale neck work as the boy swallowed. The place where he bit his throat already starting to turn purple. Just beautiful.

“As you wish, mister,” the boy said, pulling the front of his dress down along with his bra. His nipples were bigger than when he got under Brian’s care; the constant teasing since then making them fatter and more sensitive.

Timmy did as he was told, pinching his nipples between his fingers - his nails were longer now, painted hot pink - suiting a pussy boy - as he continued to bounce up and down Brian’s cock.

“Oh, yeah, just like that, bitch. Show me how much you like your titties hurting,” he said, egging him on, not like the boy needed any encouragement; he became an enthusiastic pain slut with little help from him.

Timmy bit his lip and dug his nails into his nipples, ass clenching down almost painfully around Brian.

“Yes… I love it… I love when - ah - my titties are pulled on. It’s the best… It makes my little cocklet itch to come.”

Brian had to close his eyes, feeling his orgasm building up just under his navel. Shit, there was no way he could hold on with the way Timmy was acting.

The boy probably saw him getting near to the edge, because he moaned - long and loud - and picked up the speed. His whole body was covered in a thin sheen of sweat and his ass kept constricting in the best way.

“Mister, please give me your come! My pussy is so thirsty for it, please, I need you to fill me right up…”

He might have continued, but Brian couldn’t hear him over the pleasure washing over him as his orgasm hit.

 

***

 

“Listen, sir, it’s the deal, take it or leave it,” Brian explained patiently.

“That. That was not the deal,” the customer stammered in outrage. Brian’s heart was bleeding, really.

“I don’t see why this is such a problem,” he said, reaching down to fist his hand in Timmy’s hair. Shit, that boy had a lovely mouth on him. “It’s easy. You get him on the weekends, and he stays with me for the rest of the week.”

“This is not what we agreed on,” the old man said, sounding angrier by the second. Well, better nip that in the bud.

“Yes... Well, sir, I’m pretty sure spending tax money on sex slaves is not what you agreed on with your voters either, but who am I to argue?”

There was stunned silence on the end of the line. Brian was kind of hoping the guy couldn’t hear the way Timmy kept slurping noisily around the head of his cock.

“I want to have him from Friday night to Monday morning,” the customer grit out finally. That was okay. Timmy could stand to be used by others - it would drive home that this was his place in the world now.

“That’s completely fine. I will drop him off and pick him up. Please don’t get any silly ideas, sir. As I’m sure you can imagine, I’m very well insured in case of some unfortunate emergency,” Brian told him, knowing that the guy would recognize blackmail when he heard it.

“Fine,” the old man said before hanging up on him.

That went relatively well.

Brian looked down between his legs and moaned at the sight.

Timmy was very grateful to stay. His face was a teary mess with makeup running down his cheeks and saliva smeared all over his chin.

“Well, what are you waiting for, little pussy. Show daddy how much you appreciate all he did for you.”

That was all the boy needed. He hugged Brian’s middle and practically pulled himself forward until his cock slid right into his throat. Brian loved to hear the choked off little sounds he made as he was gagging - and it did wonders to how his throat was constricting around the head of his dick.

Timmy wanted to pull back to get a breath in, but Brian palmed the back of his head keeping him there.

“Now, now. I expect a bit more dedication than that… but you may come if you can.”

The boy twitched and shuddered but didn’t try to break free, even though his oxygen was obviously running out. That was completely fine, Brian knew how much he could take.

He watched with fascination as Timmy jerked again and again, eyes rolling back to his head. Brian wasn’t even sure that the boy was even aware of when he started coming on the dirty floor under his knees.

But, hey, an orgasm was happening, so it still counted as a reward, right?

**Author's Note:**

> Or you can hit me up at udunie.tumblr.com
> 
> Also, comments are love!


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